Condensed cyclic compound, composition including the condensed cyclic compound, and organic light-emitting device including the composition

ABSTRACT

A condensed cyclic compound represented by Formula 1 and including 9 to 60 aromatic rings:wherein A, L, and n are the same as described in the specification.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. application Ser. No.16/217,194, filed on Dec. 12, 2018, which claims priority to JapanesePatent Application No. 2017-244291, filed on Dec. 20, 2017, in theJapanese Patent Office and Korean Patent Application No.10-2018-0076110, filed on Jun. 29, 2018, in the Korean IntellectualProperty Office, and all the benefits accruing therefrom under 35 U.S.C.§ 119, the contents of which are incorporated herein in their entiretiesby reference.

BACKGROUND 1. Field

One or more embodiments relate to a condensed cyclic compound, acomposition including the condensed cyclic compound, and an organiclight-emitting device including the condensed cyclic compound.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices, whichhave wide viewing angles, high contrast ratios, short response times, aswell as excellent characteristics in terms of brightness, drivingvoltage, and response speed, and which produce full-color images.

In an example, an organic light-emitting device includes an anode, acathode, and an organic layer disposed between the anode and thecathode, wherein the organic layer includes an emission layer. A holetransport region may be disposed between the anode and the emissionlayer, and an electron transport region may be disposed between theemission layer and the cathode. Holes provided from the anode may movetoward the emission layer through the hole transport region, andelectrons provided from the cathode may move toward the emission layerthrough the electron transport region. Carriers, such as holes andelectrons, recombine in the emission layer to produce excitons. Theseexcitons transit from an excited state to a ground state, therebygenerating light.

Various types of organic light emitting devices are known. However,there still remains a need in OLEDs having low driving voltage, highefficiency, high brightness, and long lifespan.

SUMMARY

Aspects of the present disclosure provide a condensed cyclic compound, acomposition including the condensed cyclic compound, and an organiclight-emitting device including the condensed cyclic compound.

The organic light-emitting device including the condensed cycliccompound may provide high current efficiency and a long lifespan. Inaddition, the condensed cyclic compound may provide characteristicssuitable for use in a solution coating.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

An aspect provides a condensed cyclic compound represented by Formula 1and including 9 to 60 aromatic rings:

In Formulae 1 and 10,

-   -   A may be a group represented by Formula 10,    -   n may be selected from 1, 2, 3, and 4,    -   L may be hydrogen, a single bond or a linking group,    -   X₁₁ may be an oxygen atom or a sulfur atom,    -   X₁₂ may be selected from N and C(R₁₂), X₁₃ may be selected from        N and C(R₁₃), X₁₄ may be selected from N and C(R₁₄), X₁₅ may be        selected from N and C(R₁₅), X₁₆ may be selected from N and        C(R₁₆), and X₁₇ may be selected from N and C(R₁₇),    -   L₁₁ and L₁₂ are each independently selected from a single bond,        a substituted or unsubstituted carbocyclic group having 5 to 60        ring-forming carbon atoms, and a substituted or unsubstituted        heterocyclic group having 5 to 60 ring-forming atoms,    -   a11 and a12 may each independently be selected from 0, 1, 2, 3,        and 4,    -   HT may be selected from a substituted or unsubstituted carbazole        group, a substituted or unsubstituted azacarbazole group, a        substituted or unsubstituted benzocarbazole group, a substituted        or unsubstituted hydrocarbazole group, a substituted or        unsubstituted acridine group, a substituted or unsubstituted        indole group, a substituted or unsubstituted xanthene group, a        substituted or unsubstituted phenoxazine group, and a        substituted or unsubstituted diphenyl amine group, and two or        more substituents included in HT may optionally be linked to        form a ring,    -   p may be selected from 0, 1, 2, 3, and 4,    -   ET may be a substituted or unsubstituted nitrogen-containing        heteroaryl group having 5 to 60 ring-forming atoms, q may be        selected from 0, 1, 2, 3, and 4,    -   R₁₁ and R₁₈ may each independently be selected from hydrogen,        deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted aryl        group having 6 to 60 ring-forming carbon atoms, and a        substituted or unsubstituted heteroaryl group having 5 to 60        ring-forming atoms,    -   b11 and b18 may each independently be selected from 0, 1, 2, 3,        4, and 5,    -   R₁₂ to R₁₇ may each independently be selected from hydrogen,        deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted aryl        group having 6 to 60 ring-forming carbon atoms, and a        substituted or unsubstituted heteroaryl group having 5 to 60        ring-forming atoms, and two neighboring groups selected from R₁₂        to R₁₇ may optionally be linked to form a ring,    -   m11 and m12 may each independently be selected from 1, 2, 3, and        4,    -   wherein, when n is 1, p is selected from 1, 2, 3, and 4, and q        is selected from 1, 2, 3, and 4, and    -   wherein the valence of the group represented by Formula 10 is        determined by n and L in Formula 1.

Another aspect provides a composition including at least one of acondensed cyclic compound represented by Formula 1.

Another aspect provides an organic light-emitting device including:

-   -   a first electrode;    -   a second electrode; and    -   an organic layer disposed between the first electrode and the        second electrode, wherein the organic layer includes an emission        layer, and wherein the organic layer includes at least one of        the condensed cyclic compound.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the FIGURE which is a schematic view of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the FIGURES, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawings, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the FIGURES, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of,” whenpreceding a list of elements, modify the entire list of elements and donot modify the individual elements of the list.

It will be understood that when an element is referred to as being “on”another element, it can be directly in contact with the other element orintervening elements may be present therebetween. In contrast, when anelement is referred to as being “directly on” another element, there areno intervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers, and/or sections, these elements, components, regions, layers,and/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer, orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that theterms “comprises” and/or “comprising,” or “includes” and/or “including”when used in this specification, specify the presence of statedfeatures, regions, integers, steps, operations, elements, and/orcomponents, but do not preclude the presence or addition of one or moreother features, regions, integers, steps, operations, elements,components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system). For example, “about” can mean within one or morestandard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

Condensed Cyclic Compound

A condensed cyclic compound according to an embodiment is represented byFormula 1:

In Formula 1, A may be a group represented by Formula 10, n may beselected from 1, 2, 3, and 4, and L may be hydrogen, a single bond or alinking group:

In Formula 10, X₁₁ to X₁₇, L₁₁, L₁₂, a11, a12, ET, HT, p, q, R₁₁, R₁₈,b11, b18, m11, and m12 may each independently be the same as describedherein.

The condensed cyclic compound represented by Formula 1 includes 9 to 60aromatic rings. The number of the aromatic rings in a term “9 to 60aromatic rings” is obtained by counting the number of the single6-membered aromatic rings in the condensed cyclic compound. Since thecondensed cyclic compound represented by Formula 1 essentially includes9 to 60 aromatic rings, the condensed cyclic compound may have improvedsolubility in an organic solvent. Since a 6-membered aromatic ring islinked in a chain shape, the degree of freedom of the condensed cycliccompound increases, thereby improving the solubility in the organicsolvent. Therefore, since it is advantageous to a solution process, itis possible to provide a layer (or a thin film) having improvedfilm-forming characteristics.

Therefore, even when an organic light-emitting device is manufactured byusing solution coating, the performance (for example, currentefficiency, lifespan, or the like) of the organic light-emitting devicemay be maintained or improved. Consequently, the organic light-emittingdevice may be manufactured without using expensive vacuum deposition. Inparticular, it may be advantageous to manufacturing a large-scaleorganic light-emitting device.

The term “aromatic ring” as used herein refers to a ring structurehaving aromaticity and may refer to a structure having (4n+2) πelectrons (n is an integer of 1 or more). The aromatic ring may haveonly a carbon atom, or may further include heterogeneous elements. Inaddition, the aromatic ring may be a single cyclic structure includingonly one ring, or may be a multi cyclic structure.

For example, the condensed cyclic compound may include 10 or more, 11 ormore, or 12 or more aromatic rings, but embodiments of the presentdisclosure are not limited thereto.

In an embodiment, the condensed cyclic compound may include 10 to 30aromatic rings, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, the condensed cyclic compound may include 9to 60 6-membered aromatic rings (for example, a benzene ring, a pyridinering, a pyrimidine ring, or the like), but embodiments of the presentdisclosure are not limited thereto.

For example, the condensed cyclic compound may have a molecular weightof about 850 Daltons to about 3,000 Daltons, but embodiments of thepresent disclosure are not limited thereto. While not wishing to bebound by theory, it is understood that when satisfying theabove-described range, the solubility of the condensed cyclic compoundis improved, thereby providing a thin film having high performance.

For example, the solubility of the condensed cyclic compound to anester-based organic solvent at room temperature (about 20° C.) may be0.5 percent by weight (weight %) or more, but embodiments of the presentdisclosure are not limited thereto.

For example, the solubility may be 1 weight % or more, but embodimentsof the present disclosure are not limited thereto. In particular, thesolubility to methyl benzoate at room temperature may be 0.5 weight % ormore, but embodiments of the present disclosure are not limited thereto.

For example, in Formula 1, n may be selected from 1 and 2, butembodiments of the present disclosure are not limited thereto. When n is1, the condensed cyclic compound may be a monomer, L may be hydrogen,the condensed cyclic compound may have a structure such as A-H. When nis two or more, L may be a n-valent linking group linked to groups A inthe number of n. When n is two or more, a plurality of groups A may beidentical to or different from each other. When n is 2 and L is a singlebond, two same or different groups A are linked via the single bond toform the condensed cyclic compound.

For example, L in Formula 1 may be selected from hydrogen, a singlebond, a substituted or unsubstituted carbocyclic group having 5 to 60ring-forming carbon atoms, and a substituted or unsubstitutedheterocyclic group having 5 to 60 ring-forming atoms, but embodiments ofthe present disclosure are not limited thereto.

In an embodiment, L in Formula 1 may be selected from hydrogen, a singlebond, a substituted or unsubstituted benzene group, a substituted orunsubstituted biphenyl group, a substituted or unsubstituted terphenylgroup, and a substituted or unsubstituted carbazole group, butembodiments of the present disclosure are not limited thereto.

In Formula 10, X₁₁ may be an oxygen atom or a sulfur atom.

In Formula 10, X₁₂ may be selected from N and C(R₁₂), X₁₃ may beselected from N and C(R₁₃), X₁₄ may be selected from N and C(R₁₄), X₁₅may be selected from N and C(R₁₅), X₁₆ may be selected from N andC(R₁₆), and X₁₇ may be selected from N and C(R₁₇).

For example, in Formula 10, X₁₂ may be C(R₁₂), X₁₃ may be C(R₁₃), X₁₄may be C(R₁₄), X₁₅ may be C(R₁₅), X₁₆ may be C(R₁₆), and X₁₇ may beC(R₁₇), but embodiments of the present disclosure are not limitedthereto.

In Formula 10, L₁₁ and L₁₂ may each independently be selected from asingle bond, a substituted or unsubstituted carbocyclic group having 5to 60 ring-forming carbon atoms, and a substituted or unsubstitutedheterocyclic group having 5 to 60 ring-forming atoms.

For example, L₁₁ and L₁₂ in Formula 10 may each independently beselected from a single bond, a substituted or unsubstituted benzenegroup, a substituted or unsubstituted indene group, a substituted orunsubstituted naphthalene group, a substituted or unsubstitutedacenaphthalene group, a substituted or unsubstituted biphenyl group, asubstituted or unsubstituted terphenyl group, a substituted orunsubstituted tetraphenyl group, a substituted or unsubstituted fluorenegroup, a substituted or unsubstituted spiro-bifluorene group, asubstituted or unsubstituted phenanthrene group, a substituted orunsubstituted anthracene group, a substituted or unsubstitutedfluoranthene group, a substituted or unsubstituted triphenylene group, asubstituted or unsubstituted pyrene group, a substituted orunsubstituted chrysene group, a substituted or unsubstituted perylenegroup, a substituted or unsubstituted benzofluorene group, a substitutedor unsubstituted pyrrole group, a substituted or unsubstituted imidazolegroup, a substituted or unsubstituted pyrazole group, a substituted orunsubstituted triazole group, a substituted or unsubstituted pyridinegroup, a substituted or unsubstituted pyrazine group, a substituted orunsubstituted pyrimidine group, a substituted or unsubstitutedpyridazine group, a substituted or unsubstituted triazine group, asubstituted or unsubstituted furan group, a substituted or unsubstitutedthiophene group, a substituted or unsubstituted oxazole group, asubstituted or unsubstituted isoxazole group, a substituted orunsubstituted thiazole group, a substituted or unsubstituted isothiazolegroup, a substituted or unsubstituted oxadiazole group, a substituted orunsubstituted isoxadiazole group, a substituted or unsubstitutedthiadiazole group, a substituted or unsubstituted isothiadiazole group,a substituted or unsubstituted pyran group, a substituted orunsubstituted indazole group, a substituted or unsubstituted purinegroup, a substituted or unsubstituted quinoline group, a substituted orunsubstituted isoquinoline group, a substituted or unsubstitutedbenzoquinoline group, a substituted or unsubstituted phthalazine group,a substituted or unsubstituted naphthyridine group, a substituted orunsubstituted quinoxaline group, a substituted or unsubstitutedquinazoline group, a substituted or unsubstituted cinnoline group, asubstituted or unsubstituted phenanthridine group, a substituted orunsubstituted acridine group, a substituted or unsubstitutedphenanthroline group, a substituted or unsubstituted phenazine group, asubstituted or unsubstituted benzoxazole group, a substituted orunsubstituted benzothiazole group, a substituted or unsubstitutedbenzimidazole group, a substituted or unsubstituted isoindole group, asubstituted or unsubstituted indole group, a substituted orunsubstituted benzofuran group, a substituted or unsubstitutedbenzothiophene group, a substituted or unsubstituted carbazole group, asubstituted or unsubstituted dibenzofuran group, a substituted orunsubstituted dibenzothiophene group, a substituted or unsubstitutedazadibenzofuran group, a substituted or unsubstitutedazadibenzothiophene group, a substituted or unsubstituteddiazadibenzofuran group, a substituted or unsubstituteddiazadibenzothiophene group, a substituted or unsubstituted xanthenegroup, a substituted or unsubstituted phenoxazine group, a substitutedor unsubstituted benzocarbazole group, a substituted or unsubstitutedhydrocarbazole group, a substituted or unsubstituted naphtho benzofurangroup, a substituted or unsubstituted naphtho benzothiophene group, asubstituted or unsubstituted imidazopyrimidine group, a substituted orunsubstituted imidazopyridine group, a substituted or unsubstituteddiphenylamine group, and a substituted or unsubstituted triphenylaminegroup, but embodiments of the present disclosure are not limitedthereto.

In an embodiment, L₁₁ and L₁₂ in Formula 10 may each independently beselected from a single bond, a substituted or unsubstituted benzenegroup, a substituted or unsubstituted biphenyl group, a substituted orunsubstituted terphenyl group, a substituted or unsubstitutedtetraphenyl group, a substituted or unsubstituted naphthalene group, asubstituted or unsubstituted fluorene group, a substituted orunsubstituted pyridine group, a substituted or unsubstituted pyrimidinegroup, and a substituted or unsubstituted triazine group, butembodiments of the present disclosure are not limited thereto.

In an embodiment, L₁₁ and L₁₂ in Formula 10 may each independently beselected from a single bond and a substituted or unsubstituted benzenegroup, but embodiments of the present disclosure are not limitedthereto.

In Formula 10, L₁₁ and L₁₂ may each independently have a binding site ata metha- or para-position to a 6-membered ring, but embodiments of thepresent disclosure are not limited thereto.

In Formula 10, a11 and a12 may each independently indicate therepetitions of L₁₁ and L₁₂, and may each independently be selected from0, 1, 2, 3, and 4. When a11 is 0, (L₁₁)_(a11) may be a single bond, whena11 is two or more, a plurality of groups L₁₁ may be identical to ordifferent from each other, when a12 is 0, (L₁₂)_(a12) may be a singlebond, and when a12 is two or more, a plurality of groups L₁₂ may beidentical to or different from each other.

For example, a11 and a12 in Formula 10 may each independently beselected from 1, 2, 3, and 4, but embodiments of the present disclosureare not limited thereto.

In an embodiment, a11 and a12 in Formula 10 may each independently beselected from 2, 3, and 4, but embodiments of the present disclosure arenot limited thereto.

In Formula 10, HT may be selected from a substituted or unsubstitutedcarbazole group, a substituted or unsubstituted azacarbazole group, asubstituted or unsubstituted benzocarbazole group, a substituted orunsubstituted hydrocarbazole group, a substituted or unsubstitutedacridine group, a substituted or unsubstituted indole group, asubstituted or unsubstituted xanthene group, a substituted orunsubstituted phenoxazine group, and a substituted or unsubstituteddiphenyl amine group,

-   -   wherein at least two substituents included in HT may be        optionally linked each other to form a ring.

For example, HT in Formula 10 may be selected from:

-   -   a carbazole group, an azacarbazole group, a benzocarbazole        group, a hydrocarbazole group, an acridine group, an indolyl        group, a xanthene group, a phenoxazine group, and a diphenyl        amine group; and    -   a carbazole group, an azacarbazole group, a benzocarbazole        group, a hydrocarbazole group, an acridine group, an indole        group, a xanthene group, a phenoxazine group, and a diphenyl        amine group, each substituted with at least one selected from        deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted aryl        group having 6 to 60 ring-forming carbon atoms, and a        substituted or unsubstituted heteroaryl group having 5 to 60        ring-forming atoms,    -   wherein at least two substituents included in HT may be        optionally linked each other to form a ring, but embodiments of        the present disclosure are not limited thereto.

In an embodiment, HT in Formula 10 may be represented by one selectedfrom Formulae 3-1 to 3-9, but embodiments of the present disclosure arenot limited thereto:

In Formulae 3-1 to 3-9,

-   -   X₃₁ may be selected from 0 and C(R₃₄)(R₃₅),    -   R₃₁ to R₃₅ may each independently be selected from hydrogen,        deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted aryl        group having 6 to 60 ring-forming carbon atoms, and a        substituted or unsubstituted heteroaryl group having 5 to 60        ring-forming atoms,    -   two neighboring groups selected from R₃₁ to R₃₅ may be        optionally linked each other to form a ring,    -   b31 may be selected from 1, 2, 3, 4, and 5,    -   b32 may be selected from 1, 2, 3, and 4,    -   b33 may be selected from 1, 2, and 3,    -   b34 may be selected from 1 and 2, and    -   * indicates a binding site to a neighboring atom.

In an embodiment, R₃₁ to R₃₅ in Formulae 3-1 to 3-9 may eachindependently be selected from hydrogen, deuterium, a substituted orunsubstituted phenyl group, a substituted or unsubstituted indenylgroup, a substituted or unsubstituted naphthyl group, a substituted orunsubstituted acenaphthyl group, a substituted or unsubstituted biphenylgroup, a substituted or unsubstituted terphenyl group, a substituted orunsubstituted fluorenyl group, a substituted or unsubstitutedspiro-bifluorenyl group, a substituted or unsubstituted phenanthrenylgroup, a substituted or unsubstituted anthracenyl group, a substitutedor unsubstituted fluoranthenyl group, a substituted or unsubstitutedtriphenyl group, a substituted or unsubstituted pyrenyl group, asubstituted or unsubstituted chrysenyl group, a substituted orunsubstituted perylenyl group, a substituted or unsubstitutedbenzofluorenyl group, a substituted or unsubstituted pyrrolyl group, asubstituted or unsubstituted imidazolyl group, a substituted orunsubstituted pyrazolyl group, a substituted or unsubstituted triazolylgroup, a substituted or unsubstituted pyridinyl group, a substituted orunsubstituted pyrazinyl group, a substituted or unsubstitutedpyrimidinyl group, a substituted or unsubstituted pyridazinyl group, asubstituted or unsubstituted triazinyl group, a substituted orunsubstituted furanyl group, a substituted or unsubstituted thiophenylgroup, a substituted or unsubstituted oxazolyl group, a substituted orunsubstituted isoxazolyl group, a substituted or unsubstituted thiazolylgroup, a substituted or unsubstituted isothiazolyl group, a substitutedor unsubstituted oxadiazolyl group, a substituted or unsubstitutedisoxadiazolyl group, a substituted or unsubstituted thiadiazolyl group,a substituted or unsubstituted isothiadiazolyl group, a substituted orunsubstituted pyranyl group, a substituted or unsubstituted indazolylgroup, a substituted or unsubstituted purinyl group, a substituted orunsubstituted quinolinyl group, a substituted or unsubstitutedisoquinolinyl group, a substituted or unsubstituted benzoquinolinylgroup, a substituted or unsubstituted phthalazinyl group, a substitutedor unsubstituted naphthyridinyl group, a substituted or unsubstitutedquinoxalinyl group, a substituted or unsubstituted quinazolinyl group, asubstituted or unsubstituted cinnolinyl group, a substituted orunsubstituted phenanthridinyl group, a substituted or unsubstitutedacridinyl group, a substituted or unsubstituted phenanthrolinyl group, asubstituted or unsubstituted phenazinyl group, a substituted orunsubstituted benzoxazolyl group, a substituted or unsubstitutedbenzothiazolyl group, a substituted or unsubstituted benzimidazolylgroup, a substituted or unsubstituted isoindolyl group, a substituted orunsubstituted indolyl group, a substituted or unsubstituted benzofuranylgroup, a substituted or unsubstituted benzothiophenyl group, asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted azacarbazolyl group, a substituted or unsubstituteddibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylgroup, a substituted or unsubstituted azadibenzofuranyl group, asubstituted or unsubstituted diazadibenzofuranyl group, a substituted orunsubstituted azadibenzothiophenyl group, a substituted or unsubstituteddiazadibenzothiophenyl group, a substituted or unsubstituted xanthenylgroup, a substituted or unsubstituted phenoxazinyl group, a substitutedor unsubstituted benzocarbazolyl group, a substituted or unsubstitutedhydrocarbazolyl group, a substituted or unsubstitutednaphthobenzofuranyl group, a substituted or unsubstitutednaphthobenzothiophenyl group, a substituted or unsubstitutedimidazopyrimidinyl group, a substituted or unsubstitutedimidazopyridinyl group, a substituted or unsubstituted group derivedfrom diphenylamine, and a substituted or unsubstituted group derivedfrom triphenylamine, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments R₃₁ to R₃₅ in Formulae 3-1 to 3-9 may eachindependently be selected from hydrogen, deuterium, a substituted orunsubstituted phenyl group, a substituted or unsubstituted biphenylgroup, a substituted or unsubstituted terphenyl group, a substituted orunsubstituted tetraphenyl group, a substituted or unsubstituted naphthylgroup, a substituted or unsubstituted fluorenyl group, a substituted orunsubstituted phenanthrenyl group, a substituted or unsubstitutedpyridinyl group, a substituted or unsubstituted pyrazinyl group, asubstituted or unsubstituted pyrimidinyl group, a substituted orunsubstituted pyridazinyl group, and a substituted or unsubstitutedtriazinyl group, but embodiments of the present disclosure are notlimited thereto.

in an embodiment, when HT in Formula 10 is a substituted orunsubstituted azacarbazole group, HT may be a group derived fromcompounds represented by the following formulae, but embodiments of thepresent disclosure are not limited thereto:

Here, two groups H may each independently be replaced with a bindingsite to a neighboring atom.

In an embodiment, when HT in Formula 10 is a substituted orunsubstituted benzocarbazole group, HT may be a group derived fromcompounds represent by Formulae 4-1 to 4-5, but embodiments of thepresent disclosure are not limited thereto:

In Formulae 4-1 to 4-5, two groups H may each independently be replacedwith a binding site to a neighboring atom.

In an embodiment, when HT in Formula 10 is a substituted orunsubstituted hydrocarbazole group, HT may be a group derived fromcompounds represent by Formulae 4-6 and 4-7, but embodiments of thepresent disclosure are not limited thereto:

In Formulae 4-6 and 4-7, 2 two groups H may each independently bereplaced with a binding site to a neighboring atom.

In an embodiment, when HT in Formula 10 is a substituted orunsubstituted acridine group, HT may be a group derived from a compoundrepresent by Formula 4-8, but embodiments of the present disclosure arenot limited thereto:

In Formula 4-8,

-   -   R₄₁ and R₄₂ may each independently be selected from hydrogen,        deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted        C₁₋₁₀ alkyl group, a substituted or unsubstituted C₃₋₁₀        cycloalkyl group, a substituted or unsubstituted aryl group        having 6 to 60 ring-forming carbon atoms, and a substituted or        unsubstituted heteroaryl group having 5 to 60 ring-forming        atoms, and    -   two groups H may each independently be replaced with a binding        site to a neighboring atom.

In an embodiment, when HT in Formula 10 is a substituted orunsubstituted indole group, HT may be a group derived from a compoundrepresented by Formula 4-9, but embodiments of the present disclosureare not limited thereto:

In Formula 4-9, two groups H may each independently be replaced with abinding site to a neighboring atom.

In an embodiment, when HT in Formula 10 is a substituted orunsubstituted xanthene group, HT may be a group derived from a compoundrepresented by Formula 4-10, but embodiments of the present disclosureare not limited thereto:

In Formula 4-10,

-   -   R₄₁ and R₄₂ may each independently be selected from hydrogen,        deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted        C₁₋₁₀ alkyl group, a substituted or unsubstituted C₃₋₁₀        cycloalkyl group, a substituted or unsubstituted aryl group        having 6 to 60 ring-forming carbon atoms, and a substituted or        unsubstituted heteroaryl group having 5 to 60 ring-forming        atoms, and    -   two groups H may each independently be replaced with a binding        site to a neighboring atom.

In an embodiment, when HT in Formula 10 is a substituted orunsubstituted phenoxazine group, HT may be a group derived from acompound represented by Formula 4-11, but embodiments of the presentdisclosure are not limited thereto:

In Formula 4-11, two groups H may each independently be replaced with abinding site to a neighboring atom.

In Formula 10, p indicates the number of repetitions of HT, and may beselected from 0, 1, 2, 3, and 4. When p is two or more, a plurality ofgroups HT may be identical to or different from each other.

For example, p in Formula 10 may be selected from 0 and 1, butembodiments of the present disclosure are not limited thereto.

In Formula 10, ET may be a substituted or unsubstitutednitrogen-containing heteroaryl group having 5 to 60 ring-forming atoms.For example, ET in Formula 10 may have a monocyclic or polycyclicstructure, wherein the structure may be a 5-membered ring structure, a6-membered ring structure, a structure in which at least two 5-memberedrings condensed, a structure in which at least two 6-membered rings arecondensed, or a structure in which at least one 5-membered rings and atleast one 6-membered rings are condensed, but embodiments of the presentdisclosure are not limited thereto.

For example, ET in Formula 10 may be selected from a substituted orunsubstituted pyrrole group, a substituted or unsubstituted pyrazolegroup, a substituted or unsubstituted imidazole group, a substituted orunsubstituted triazole group, a substituted or unsubstituted pyridinegroup, a substituted or unsubstituted pyrimidine group, a substituted orunsubstituted pyridazine group, a substituted or unsubstituted pyrazinegroup, a substituted or unsubstituted triazine group, a substituted orunsubstituted indole group, a substituted or unsubstituted isoindolegroup, a substituted or unsubstituted indazole group, a substituted orunsubstituted benzimidazole group, a substituted or unsubstitutedquinoline group, a substituted or unsubstituted isoquinoline group, asubstituted or unsubstituted phthalazine group, a substituted orunsubstituted naphthyridine group, a substituted or unsubstitutedcinnoline group, a substituted or unsubstituted quinoxaline group, asubstituted or unsubstituted quinazoline group, and a substituted orunsubstituted imidazopyridine group, but embodiments of the presentdisclosure are not limited thereto.

In an embodiment, ET in Formula 10 may be selected from:

-   -   a pyrrole group, a pyrazole group, an imidazole group, a        triazole group, a pyridine group, a pyrimidine group, a        pyridazine group, a pyrazine group, a triazine group, an indole        group, an isoindole group, an indazole group, a benzimidazole        group, a quinoline group, an isoquinoline group, a phthalazine        group, a naphthyridine group, a cinnoline group, a quinoxaline        group, a quinazoline group, and an imidazopyridine group; and    -   a pyrrole group, a pyrazole group, an imidazole group, a        triazole group, a pyridine group, a pyrimidine group, a        pyridazine group, a pyrazine group, a triazine group, an indole        group, an isoindole group, an indazole group, a benzimidazole        group, a quinoline group, an isoquinoline group, a phthalazine        group, a naphthyridine group, a cinnoline group, a quinoxaline        group, a quinazoline group, and an imidazopyridine group, each        substituted with at least one selected from deuterium, —F, —Cl,        —Br, —I, a substituted or unsubstituted aryl group having 6 to        60 ring-forming carbon atoms, and a substituted or unsubstituted        heteroaryl group having 5 to 60 ring-forming atoms, but        embodiments of the present disclosure are not limited thereto.

In an embodiment, ET in Formula 10 may be a group represented by oneselected from Formulae 2-1 to 2-4, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 2-1 to 2-4,

-   -   R₂₁ may be selected from deuterium, —F, —Cl, —Br, —I, a        substituted or unsubstituted aryl group having 6 to 60        ring-forming carbon atoms, and a substituted or unsubstituted        heteroaryl group having 5 to 60 ring-forming atoms,    -   two neighboring groups selected from groups R₂₁ may be        optionally linked each other to form a ring,    -   b21 may be selected from 1, 2, and 3,    -   b22 may be selected from 1 and 2, and    -   * indicates a binding site to a neighboring atom.

In an embodiment, R₂₁ in Formulae 2-1 to 2-4 may be selected fromhydrogen, deuterium, a substituted or unsubstituted phenyl group, asubstituted or unsubstituted indenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted acenaphthylgroup, a substituted or unsubstituted biphenyl group, a substituted orunsubstituted terphenyl group, a substituted or unsubstituted fluorenylgroup, a substituted or unsubstituted spiro-bifluorenyl group, asubstituted or unsubstituted phenanthrenyl group, a substituted orunsubstituted anthracenyl group, a substituted or unsubstitutedfluoranthenyl group, a substituted or unsubstituted triphenyl group, asubstituted or unsubstituted pyrenyl group, a substituted orunsubstituted chrysenyl group, a substituted or unsubstituted perylenylgroup, a substituted or unsubstituted benzofluorenyl group, asubstituted or unsubstituted pyrrolyl group, a substituted orunsubstituted imidazolyl group, a substituted or unsubstituted pyrazolylgroup, a substituted or unsubstituted triazolyl group, a substituted orunsubstituted pyridinyl group, a substituted or unsubstituted pyrazinylgroup, a substituted or unsubstituted pyrimidinyl group, a substitutedor unsubstituted pyridazinyl group, a substituted or unsubstitutedtriazinyl group, a substituted or unsubstituted furanyl group, asubstituted or unsubstituted thiophenyl group, a substituted orunsubstituted oxazolyl group, a substituted or unsubstituted isoxazolylgroup, a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted isothiazolyl group, a substituted or unsubstitutedoxadiazolyl group, a substituted or unsubstituted isoxadiazolyl group, asubstituted or unsubstituted thiadiazolyl group, a substituted orunsubstituted isothiadiazolyl group, a substituted or unsubstitutedpyranyl group, a substituted or unsubstituted indazolyl group, asubstituted or unsubstituted purinyl group, a substituted orunsubstituted quinolinyl group, a substituted or unsubstitutedisoquinolinyl group, a substituted or unsubstituted benzoquinolinylgroup, a substituted or unsubstituted phthalazinyl group, a substitutedor unsubstituted naphthyridinyl group, a substituted or unsubstitutedquinoxalinyl group, a substituted or unsubstituted quinazolinyl group, asubstituted or unsubstituted cinnolinyl group, a substituted orunsubstituted phenanthridinyl group, a substituted or unsubstitutedacridinyl group, a substituted or unsubstituted phenanthrolinyl group, asubstituted or unsubstituted phenazinyl group, a substituted orunsubstituted benzoxazolyl group, a substituted or unsubstitutedbenzothiazolyl group, a substituted or unsubstituted benzimidazolylgroup, a substituted or unsubstituted isoindolyl group, a substituted orunsubstituted indolyl group, a substituted or unsubstituted benzofuranylgroup, a substituted or unsubstituted benzothiophenyl group, asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted azacarbazolyl group, a substituted or unsubstituteddibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylgroup, a substituted or unsubstituted azadibenzofuranyl group, asubstituted or unsubstituted diazadibenzofuranyl group, a substituted orunsubstituted azadibenzothiophenyl group, a substituted or unsubstituteddiazadibenzothiophenyl group, a substituted or unsubstituted xanthenylgroup, a substituted or unsubstituted phenoxazinyl group, a substitutedor unsubstituted benzocarbazolyl group, a substituted or unsubstitutedhydrocarbazolyl group, a substituted or unsubstitutednaphthobenzofuranyl group, a substituted or unsubstitutednaphthobenzothiophenyl group, a substituted or unsubstitutedimidazopyrimidinyl group, a substituted or unsubstitutedimidazopyridinyl group, a substituted or unsubstituted group derivedfrom diphenylamine, and a substituted or unsubstituted group derivedfrom triphenylamine, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, R₂₁ in Formulae 2-1 to 2-4 may eachindependently be selected from hydrogen, deuterium, a substituted orunsubstituted phenyl group, a substituted or unsubstituted biphenylgroup, a substituted or unsubstituted terphenyl group, a substituted orunsubstituted tetraphenyl group, a substituted or unsubstituted naphthylgroup, a substituted or unsubstituted fluorenyl group, a substituted orunsubstituted phenanthrenyl group, a substituted or unsubstitutedpyridinyl group, a substituted or unsubstituted pyrazinyl group, asubstituted or unsubstituted pyrimidinyl group, a substituted orunsubstituted pyridazinyl group, and a substituted or unsubstitutedtriazinyl group, but embodiments of the present disclosure are notlimited thereto.

In Formula 10, q indicates the number of the repetitions of ET, and maybe selected from 0, 1, 2, 3, and 4. When q is two or more, a pluralityof groups ET may be identical to or different from each other.

For example, q in Formula 10 may be selected from 0 and 1, butembodiments of the present disclosure are not limited thereto.

In Formula 10, R₁₁ and R₁₈ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a substituted or unsubstitutedaryl group having 6 to 60 ring-forming carbon atoms, and a substitutedor unsubstituted heteroaryl group having 5 to 60 ring-forming atoms.

In Formula 10, R₁₂ to R₁₇ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a substituted or unsubstitutedaryl group having 6 to 60 ring-forming carbon atoms, and a substitutedor unsubstituted heteroaryl group having 5 to 60 ring-forming atoms, andtwo neighboring groups selected from R₁₂ to R₁₇ may be optionally linkedeach other to form a ring.

For example, R₁₁ to R₁₈ in Formula 10 may each independently be selectedfrom hydrogen, deuterium, a substituted or unsubstituted phenyl group, asubstituted or unsubstituted indenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted acenaphthylgroup, a substituted or unsubstituted biphenyl group, a substituted orunsubstituted terphenyl group, a substituted or unsubstituted fluorenylgroup, a substituted or unsubstituted spiro-bifluorenyl group, asubstituted or unsubstituted phenanthrenyl group, a substituted orunsubstituted anthracenyl group, a substituted or unsubstitutedfluoranthenyl group, a substituted or unsubstituted triphenyl group, asubstituted or unsubstituted pyrenyl group, a substituted orunsubstituted chrysenyl group, a substituted or unsubstituted perylenylgroup, a substituted or unsubstituted benzofluorenyl group, asubstituted or unsubstituted pyrrolyl group, a substituted orunsubstituted imidazolyl group, a substituted or unsubstituted pyrazolylgroup, a substituted or unsubstituted triazolyl group, a substituted orunsubstituted pyridinyl group, a substituted or unsubstituted pyrazinylgroup, a substituted or unsubstituted pyrimidinyl group, a substitutedor unsubstituted pyridazinyl group, a substituted or unsubstitutedtriazinyl group, a substituted or unsubstituted furanyl group, asubstituted or unsubstituted thiophenyl group, a substituted orunsubstituted oxazolyl group, a substituted or unsubstituted isoxazolylgroup, a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted isothiazolyl group, a substituted or unsubstitutedoxadiazolyl group, a substituted or unsubstituted isoxadiazolyl group, asubstituted or unsubstituted thiadiazolyl group, a substituted orunsubstituted isothiadiazolyl group, a substituted or unsubstitutedpyranyl group, a substituted or unsubstituted indazolyl group, asubstituted or unsubstituted purinyl group, a substituted orunsubstituted quinolinyl group, a substituted or unsubstitutedisoquinolinyl group, a substituted or unsubstituted benzoquinolinylgroup, a substituted or unsubstituted phthalazinyl group, a substitutedor unsubstituted naphthyridinyl group, a substituted or unsubstitutedquinoxalinyl group, a substituted or unsubstituted quinazolinyl group, asubstituted or unsubstituted cinnolinyl group, a substituted orunsubstituted phenanthridinyl group, a substituted or unsubstitutedacridinyl group, a substituted or unsubstituted phenanthrolinyl group, asubstituted or unsubstituted phenazinyl group, a substituted orunsubstituted benzoxazolyl group, a substituted or unsubstitutedbenzothiazolyl group, a substituted or unsubstituted benzimidazolylgroup, a substituted or unsubstituted isoindolyl group, a substituted orunsubstituted indolyl group, a substituted or unsubstituted benzofuranylgroup, a substituted or unsubstituted benzothiophenyl group, asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted azacarbazolyl group, a substituted or unsubstituteddibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylgroup, a substituted or unsubstituted azadibenzofuranyl group, asubstituted or unsubstituted diazadibenzofuranyl group, a substituted orunsubstituted azadibenzothiophenyl group, a substituted or unsubstituteddiazadibenzothiophenyl group, a substituted or unsubstituted xanthenylgroup, a substituted or unsubstituted phenoxazinyl group, a substitutedor unsubstituted benzocarbazolyl group, a substituted or unsubstitutedhydrocarbazolyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted imidazopyrimidinylgroup, a substituted or unsubstituted imidazopyridinyl group, asubstituted or unsubstituted group derived from diphenyl amine, and asubstituted or unsubstituted group derived from triphenylamine, butembodiments of the present disclosure are not limited thereto.

In an embodiment, R₁₁ to R₁₈ in Formula 10 may each independently beselected from hydrogen, deuterium, a substituted or unsubstituted phenylgroup, a substituted or unsubstituted biphenyl group, a substituted orunsubstituted terphenyl group, a substituted or unsubstitutedtetraphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted fluorenyl group, a substituted orunsubstituted phenanthrenyl group, a substituted or unsubstitutedpyridinyl group, a substituted or unsubstituted pyrazinyl group, asubstituted or unsubstituted pyrimidinyl group, a substituted orunsubstituted pyridazinyl group, a substituted or unsubstitutedtriazinyl group, a substituted or unsubstituted carbazolyl group, asubstituted or unsubstituted azacarbazolyl group, a substituted orunsubstituted benzocarbazolyl group, a substituted or unsubstitutedhydrocarbazolyl group, a substituted or unsubstituted acridinyl group, asubstituted or unsubstituted indolyl group, a substituted orunsubstituted xanthenyl group, a substituted or unsubstitutedphenoxazinyl group, a substituted or unsubstituted group derived fromdiphenyl amine, and a substituted or unsubstituted group derived fromtriphenylamine, but embodiments of the present disclosure are notlimited thereto.

In an embodiment, R₁₁ to R₁₈ in Formula 10 may each independently beselected from hydrogen, deuterium, a substituted or unsubstituted phenylgroup, a substituted or unsubstituted biphenyl group, a substituted orunsubstituted terphenyl group, a substituted or unsubstitutedtetraphenyl group, a substituted or unsubstituted naphthyl group, asubstituted or unsubstituted fluorenyl group, a substituted orunsubstituted pyridinyl group, and a substituted or unsubstitutedpyrimidinyl group, but embodiments of the present disclosure are notlimited thereto.

In Formula 10, b11 and b18 respectively indicate the number of groupsR₁₁ and groups R₁₈, and b11 and b18 may each independently be selectedfrom 0, 1, 2, 3, 4, and 5.

In Formula 10, m11 and m12 may each independently be selected from 1, 2,3, and 4.

For example, in Formula 10, m11 and m12 may each independently beselected from 1 and 2, but embodiments of the present disclosure are notlimited thereto.

In Formula 1, when n is 1, p may be selected from 1, 2, 3, and 4, and qmay be selected from 1, 2, 3, and 4.

In an embodiment, the condensed cyclic compound may be represented byone selected from Formulae 1-1 to 1-6, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 1-1 to 1-6,

-   -   L may be the same as described in Formula 1,    -   X₁₁, R₁₁ to R₁₈, ET, HT, L₁₁, L₁₂, a11, and a12 may each        independently be the same as described in Formula 10,    -   X_(11 a) and X_(11b) may each independently be the same as        described in connection with X₁₁ in Formula 10,    -   R_(12a), R_(12b), R_(13a), R_(13b), R_(14a), R_(14b), R_(15a),        R_(15b), R_(16a), R_(16b), R_(17a), R_(17b), R_(18a), and        R_(18b) may each independently be the same as described in        connection with R₁₁ in Formula 10,    -   ET_(a) and ET_(b) may each independently be the same as        described in connection with ET in Formula 10,    -   HT_(a) and HT_(b) may each independently be the same as        described in connection with HT in Formula 10,    -   L_(11a) and L_(11b) are each independently the same as described        in connection with L₁₁ in Formula 10,    -   L_(12a) and L_(12b) are each independently the same as described        in connection with L₁₂ in Formula 10,    -   a_(11a) and a_(11b) are each independently the same as described        in connection with a₁₁ in Formula 10, and    -   a_(12a) and a_(12b) are each independently the same as described        in connection with a₁₂ in Formula 10.

In one or more embodiments, the condensed cyclic compound may beselected from Compounds 1-1 to 1-24 and 2-1 to 2-14, but embodiments ofthe present disclosure are not limited thereto:

Compounds 1-1 to 1-24 correspond to an embodiment in which n in Formula1 is 1, and Compounds 2-1 to 2-14 correspond to an embodiment in which nFormula 1 is 2.

The condensed cyclic compound represented by Formula 1 may be includedin an organic layer disposed between a pair of electrodes of an organiclight-emitting device. For example, the condensed cyclic compoundrepresented by Formula 1 may be included in an emission layer and may besuitable as a host. In an embodiment, the condensed cyclic compoundrepresented by Formula 1 may be suitable as a charge transport material.

The condensed cyclic compound represented by Formula 1 may besynthesized by using a known organic synthesis method. A method ofsynthesizing the condensed cyclic compound represented by Formula 1 canbe understood by a person skilled in the art by referring to Examplesprovided below.

Composition

Hereinafter, a composition according to an embodiment will be describedin detail.

The composition may include at least one of the condensed cycliccompound described above.

For example, the composition may further include at least one of a firstcompound represented by one selected from Formulae 5 and 6:

In Formulae 5 and 6,

-   -   X₅₁ may be N or C(R₅₁); X₅₂ may be N or C(R₅₂); X₅₃ may be N or        C(R₅₃); X₅₄ may be N or C(R₅₄); X₅₅ may be N or C(R₅₅); X₅₅ may        be N or C(R₅₆); X₅₇ may be N or C(R₅₇); and X₅₈ may be N or        C(R₅₈),    -   R₅₁ to R₅₈ and R₆₁ to R₇₂ may each independently be selected        from hydrogen, deuterium, a substituted or unsubstituted C₆-C₆₀        aryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl        group, a substituted or unsubstituted monovalent non-aromatic        condensed polycyclic group, and a substituted or unsubstituted        monovalent non-aromatic condensed heteropolycyclic group, and    -   R₅₉ may be selected from a substituted or unsubstituted aryl        group having 6 to 60 ring-forming carbon atoms, a substituted or        unsubstituted heteroaryl group having 5 to 60 ring-forming        atoms, a substituted or unsubstituted monovalent non-aromatic        condensed polycyclic group, and a substituted or unsubstituted        monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formulae 5 and 6, two neighboring groups selected fromR₅₁ to R₅₈ and R₆₁ to R₇₂ may optionally be linked to form a ring, butembodiments of the present disclosure are not limited thereto.

When the composition includes the condensed cyclic compound and thefirst compound, the composition may be excellent in terms of electroninjection and/or electron transport, and the composition may be used foran electron injection layer, an electron transport layer, and/or anemission layer of an organic light-emitting device.

The composition may further include a light-emitting material.

The light-emitting material is not particularly limited as long as thelight-emitting material has a light-emitting function, and may be afluorescent dopant, a phosphorescent dopant, a quantum dot, or the like.For example, the light-emitting material may be a phosphorescent dopant,but embodiments of the present disclosure are not limited thereto.

The fluorescent dopant is a compound that can emit light from singletexciton.

For example, the fluorescent dopant may be a perylene and a derivativethereof, a rubrene and a derivative thereof, a coumarin and a derivativethereof, or a4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) anda derivative thereof, but embodiments of the present disclosure are notlimited thereto.

The phosphorescent dopant is a compound that can emit light from tripletexciton, and may be an organometallic compound. For example, thephosphorescent dopant may be an iridium complex, such asbis[2-(4,6-difluorophenyl)pyridinate]picolinate iridium(III) (Flrpic),bis(1-phenylisoquinoline)(acetylacetonate) iridium(III)(Ir(piq)₂(acac)), tris(2-phenylpyridine) iridium(III) (Ir(ppy)₃), ortris(2-(3-p-xylyl)phenyl)pyridine iridium(III) (dopant), an osmiumcomplex, a platinum complex, or the like, but embodiments of the presentdisclosure are not limited thereto.

The quantum dot may be a nanoparticle including group II-VIsemiconductor, group III-V semiconductor, or group IV-IV semiconductor.For example, the quantum dot may be CdO, CdS, CdSe, CdTe, ZnO, ZnS,ZnSe, ZnTe, HgS, HgSe, HgTe, MgSe, MgS CdSeS, CdSeTe, CdSTe, ZnSeS,ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS,CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, GaN, GaP, GaAs,AlN, AlP, AlAs, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPAs, GaPSb,AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InPAs, InPSb, GaAlNP,SnS, SnSe, SnTe, PbS, PbSe, PbTe, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe,PbSTe, SnPbS, SnPbSe, SnPbTe, or the like, but embodiments of thepresent disclosure are not limited thereto. In addition, the diameter ofthe quantum dot is not particularly limited, but may be in a range ofabout 1 nanometer (nm) to about 20 nm. The quantum dot may be a singlecore structure, or may be a core-shell structure.

The composition may further include a solvent.

The solvent is not particularly limited as long as the solvent isdissolved in the condensed cyclic compound represented by Formula 1.

For example, the solvent may be ketone, aliphatic ester, an aromaticester, a halogenated hydrocarbon, a non-fluorinated alcohol, fluorinatedalcohol, aliphatic hydrocarbon, an aromatic hydrocarbon, or an aromatichydrocarbon substituted compound, but embodiments of the presentdisclosure are not limited thereto.

In an embodiment, the solvent may be toluene, xylene, ethylbenzene,diethylbenzene, mesitylene, propylbenzene, cyclohexylbenzene,dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene,iso-propylbiphenyl, dimethylanisole, phenyl acetate, phenyl propionicacid, methyl benzoate, ethyl benzoate, or the like, but embodiments ofthe present disclosure are not limited thereto.

The solvent may be an aromatic ester, and for example, may be methylbenzoate or ethyl benzoate, but embodiments of the present disclosureare not limited thereto.

The concentration of the composition is not particularly limited, andmay be appropriately controlled according to the purpose thereof.

In the composition, the concentration of the condensed cyclic compoundrepresented by Formula 1 may be in a range of about 0.1 weight % toabout 20 weight %, and for example, in a range of about 0.5 weight % toabout 10 weight %, but embodiments of the present disclosure are notlimited thereto. When the concentration of the condensed cyclic compoundis within this range, the coatability may be improved.

Therefore, the composition may be used as a material for forming alight-emitting device (for example, an organic light-emitting device, aquantum dot light-emitting device, or the like). For example, thecomposition may be used for an emission layer, a charge injection layer,and/or a charge transport layer of a light-emitting device. In anotherexample, the composition may be used for an emission layer of alight-emitting device. In yet another example, the composition may beused when a light-emitting device is manufactured by using solutioncoating. At this time, the current efficiency and light-emittinglifespan of the light-emitting device may be improved.

Organic Light-Emitting Device

Hereinafter, an organic light-emitting device according to an embodimentwill be described in detail with reference to the FIGURE. The FIGURE isa schematic cross-sectional view of an organic light-emitting deviceaccording to an embodiment.

The organic light-emitting device 100 according to the embodiment mayinclude a substrate 110, a first electrode 120 on the substrate 110, ahole injection layer 130 on the first electrode 120, a hole transportlayer 140 on the hole injection layer 130, an emission layer 150 on thehole transport layer 140, an electron transport layer 160 on theemission layer 150, an electron injection layer 170 on the electrontransport layer 160, and a second electrode 180 on the electroninjection layer 170.

The condensed cyclic compound represented by Formula 1, may be includedin, for example, an organic layer disposed between the first electrode120 and the second electrode 180 (for example, one selected from thehole injection layer 130, the hole transport layer 140, the emissionlayer 150, the electron transport layer 160, and the electron injectionlayer 170). For example, the condensed cyclic compound represented byFormula 1 may be included in the emission layer 150 as a host.

Alternatively, the condensed cyclic compound represented by Formula 1may be included in another organic layer other than the emission layer150. For example, the condensed cyclic compound represented by Formula 1may be included in the electron transport layer 160 and/or the electroninjection layer 170 as a charge transport material.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers between the first electrode and the secondelectrode of the organic light-emitting device. The “organic layer” mayinclude, in addition to an organic compound, an organometallic compoundincluding metal.

The expression “(an organic layer) includes at least one organometalliccompound” as used herein may include a case in which “(an organic layer)includes identical compounds represented by Formula 1” and a case inwhich “(an organic layer) includes two or more different condensedcyclic compounds represented by Formula 1.”

For example, the organic layer may include, as the condensed cycliccompound, only Compound 1-1. In this regard, Compound 1-1 may beincluded only in the emission layer of the organic light-emittingdevice. In one or more embodiments, the organic layer may include, asthe condensed cyclic compound, Compound 1-1 and Compound 1-2. In thisregard, Compound 1-1 and Compound 1-2 may be included in an identicallayer (for example, Compound 1 and Compound 2 all may exist in anemission layer).

The substrate 110 may be any substrate that is used in an organiclight-emitting device according to the related art. For example, thesubstrate 110 may be a glass substrate, a silicon substrate, or atransparent plastic substrate, each having excellent mechanicalstrength, thermal stability, surface smoothness, ease of handling, andwater resistance, but embodiments of the present disclosure are notlimited thereto.

The first electrode 120 may be formed on the substrate 110. The firstelectrode 120 may be, for example, an anode, and may be formed of amaterial with a high work function to facilitate hole injection, such asan alloy or a conductive compound. The first electrode 120 may be areflective electrode, a semi-transmissive electrode, or a transmissiveelectrode. The first electrode 120 may have a single-layered structureor a multi-layered structure including two or more layers. For example,the first electrode 120 may be a transparent electrode formed of indiumtin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zincoxide (ZnO), which has excellent transparency and conductivity. On thetransparent first electrode 120, magnesium (Mg), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), ormagnesium-silver (Mg—Ag) may be disposed, so as to form a reflectiveelectrode. In an embodiment, the first electrode 120 may have athree-layered structure of ITO/Ag/ITO, but embodiments of the presentdisclosure are not limited thereto.

The hole transport region may be disposed on the first electrode 120.

The hole transport region may include at least one selected fromselected from a hole injection layer 130, a hole transport layer 140, anelectron blocking layer (not shown), and a buffer layer (not shown).

The hole transport region may include only either a hole injection layer130 or a hole transport layer 140. In an embodiment, the hole transportregion may have a hole injection layer/hole transport layer structure ora hole injection layer/hole transport layer/electron blocking layerstructure, wherein for each structure, constituting layers aresequentially stacked from the first electrode 120 in the stated order.

The hole injection layer 130 may include at least one selected from, forexample poly(ether ketone)-containing triphenylamine (TPAPEK),4-iso-propyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (PPBI),N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), copper phthalocyanine, 4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine(NPB), 4,4′,4″-tris(diphenylamino) triphenylamine (TDATA),4,4′,4″-tris(N,N-2-naphthylphenylamino) triphenylamine (2-TNATA),polyaniline/dodecylbenzene sulphonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS),polyaniline/10-camphor sulfonic acid (PANI/CSA), andpolyaniline/poly(4-styrene sulfonate) (PANI/PSS).

The hole injection layer 130 may be formed to a thickness in a range ofabout 10 nm to about 1,000 nm, for example, about 10 nm to about 100 nm.

The hole transport layer 140 may include at least one selected from, forexample, a carbazole derivative, such as1,1-bis[(di-4-tolylamino)phenyl] cyclohexane (TAPC), N-phenylcarbazole,and polyvinylcarbazole,N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), 4,4′,4″-tris(N-carbazolyl) triphenylamine (TCTA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB),poly(9,9-dioctyl-fluorene-co-N-(4-butylphenyl)-diphenylamine (TFB), P-1,and FA-14:

Number average molecular weight M_(n)=141,000.

Weight average molecular weight M_(w)=511,000.

The hole transport layer 140 may be formed to a thickness in a range ofabout 10 nm to about 1,000 nm, for example, about 10 nm to about 150 nm.

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant. Thep-dopant may be one selected from a quinone derivative, a metal oxide,and a cyano group-containing compound, but embodiments of the presentdisclosure are not limited thereto. Non-limiting examples of thep-dopant are a quinone derivative, such as tetracyanoquinonedimethane(TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane(F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdeniumoxide; and a cyano group-containing compound, such as Compound HT-D1 orCompound HT-D2, but are not limited thereto.

Meanwhile, when the hole transport region includes a buffer layer, amaterial for the buffer layer may be selected from materials for thehole transport region described above and materials for a host to beexplained later. However, the material for the electron blocking layeris not limited thereto.

In addition, when the hole transport region includes an electronblocking layer, a material for the electron blocking layer may beselected from materials for the hole transport region described aboveand materials for a host to be explained later.

However, the material for the electron blocking layer is not limitedthereto. For example, when the hole transport region includes anelectron blocking layer, a material for the electron blocking layer maybe mCP.

The mission layer 150 may be formed on the hole transport region. Theemission layer 150 is a layer that emits light by fluorescence orphosphorescence. The emission layer 150 may include a host and/or adopant, and when included, the host may include the condensed cycliccompound represented by Formula 1. In addition, the host and/or thedopant included in the emission layer 150 may be known materials.

For example, the host may include tris(8-quinolinato)aluminium (Alq₃),4,4′-bis(carbazol-9-yl)biphenyl (CBP), poly(n-vinylcarbazole) (PVK),9,10-di(naphthalene)anthracene (ADN),4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBi)3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), distyrylarylene(DSA), 4,4′-bis(9-carbazole)-2,2′-dimethyl-bipheny (dmCBP), HT-Host-A,or HT-Host-B, but embodiments of the present disclosure are not limitedthereto:

For example, the dopant may include a perylene and a derivative thereof,a rubrene and a derivative thereof, a coumarin and a derivative thereof,4-dicyanomethylene-2-(p-dimethylaminostyryl)-6-methyl-4H-pyran (DCM) anda derivative thereof, an iridium complex, such asbis[2-(4,6-difluorophenyl)pyridinate] picolinate iridium (III) (Flrpic),bis(1-phenylisoquinoline)(acetylacetonate) iridium (III)(Ir(piq)₂(acac)), tris(2-phenylpyridine) iridium (III) (Ir(ppy)₃),tris(2-(3-p-xylyl)phenyl)pyridine iridium (III) (dopant), an osmiumcomplex, or a platinum complex, but embodiments of the presentdisclosure are not limited thereto.

When the emission layer 150 includes the host and/or the dopant, anamount of the host may be greater than that of the dopant, and an amountof the dopant may be in a range of about 0.01 parts by weight to about15 parts by weight based on 100 parts by weight of the host, butembodiments of the present disclosure are not limited thereto.

In addition, when the emission layer 150 includes the condensed cycliccompound represented by Formula 1 as an electron transporting host, aratio of the condensed cyclic compound to the entire host in theemission layer 150 may be in a range of about 1 weight % to about 99weight %, for example, about 5 weight % to about 95 weight %, forexample, about 10 weight % to about 90 weight %, but embodiments of thepresent disclosure are not limited thereto.

The emission layer 150 may be formed to a thickness in a range about 10nm to about 60 nm.

When the organic light-emitting device is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Inone or more embodiments, due to a stacked structure including a redemission layer, a green emission layer, and/or a blue emission layer,the emission layer may emit white light.

The electron transport region may be disposed on the emission layer 150.

The electron transport region may include at least one selected from ahole blocking layer (not shown), an electron transport layer 160, and anelectron injection layer 170.

For example, the electron transport region may have a hole blockinglayer/electron transport layer/electron injection layer structure or anelectron transport layer/electron injection layer structure, but thestructure of the electron transport region is not limited thereto. Theelectron transport layer may have a single-layered structure or amulti-layered structure including two or more different materials.

For example, the organic light-emitting device 100 may include, toprevent the excitons or holes from diffusing into the electron transportlayer 160, a hole blocking layer disposed between the electron transportlayer 160 and the emission layer 150. The hole blocking layer mayinclude, for example, at least one selected from an oxadiazolederivative, a triazole derivative, BCP, Bphen, and BAlq, but a materialtherefor is not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20Angstroms (Å) to about 1,000 Å, for example, about 30 Å to about 300 Å.While not wishing to be bound by theory, it is understood that when thethickness of the hole blocking layer is within these ranges, the holeblocking layer may have excellent hole blocking characteristics withouta substantial increase in driving voltage.

In an embodiment, the electron transport layer 160 may includetris(8-quinolinato) aluminium (Alq3), BAlq, a compound including apyridine ring, such as 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, acompound including a triazine ring, such as2,4,6-tris(3′-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, a compoundincluding an imidazole ring, such as2-(4-(N-phenylbenzimidazolyl-1-yl-phenyl)-9,10-dinaphthylanthracene, acompound including a triazole ring, such as TAZ and NTAZ,1,3,5-tris(N-phenyl-benzimidazol-2-yl)benzene (TPBi), BCP, or Bphen:

In one or more embodiments, the electron transport layer 160 may includea commercial product, such as KLET-01, KLET-02, KLET-03, KLET-10, orKLET-M1 (these products are available from Chemipro Kasei).

The electron transport layer 160 may further include, in addition to thematerials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complexmay include, for example, Compound ET-D1 (lithium 8-hydroxyquinolate,LiQ) or ET-D2.

The electron transport layer 160 may be formed to a thickness, forexample, in a range of about 15 nm to about 50 nm.

The electron injection layer 170 may be formed on the electron transportlayer 160.

The electron injection layer 170 may include, for example, an lithiumcompound, such as (8-hydroxyquinolinato)aithium (LiQ) and lithiumfluoride (LiF), sodium chloride (NaCl), cesium fluoride (CsF), Iithiumoxide (Li₂O), or barium oxide (BaO).

The electron injection layer 170 may be formed to a thickness in a rangeof about 0.3 nm to about 9 nm.

The second electrode 180 may be formed on the electron injection layer170.

The second electrode 180 may be a cathode and may be formed by using amaterial having a low work function among a metal, an alloy, anelectrically conductive compound, and any combination thereof. Forexample, the second electrode 180 may be formed as a reflectiveelectrode by using a metal such as lithium (Li), magnesium (Mg),aluminum (Al), and calcium (Ca), or an alloy such as aluminum-lithium(Al—Li), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag).Alternatively, the second electrode 180 may be formed as a transparentelectrode by using the metal or the alloy thin film having a thicknessof 20 nm or less, or a transparent conductive film such as indium tinoxide (In₂O₃—SnO₂) and indium zinc oxide (In₂O₃—ZnO).

In addition, the stacked structure of the organic light-emitting device100 according to the embodiment is not limited to the above-describedstacked structure.

The organic light-emitting device 100 according to the embodiment may beformed in other known stacked structures. For example, in the organiclight-emitting device 100, at least one of the hole injection layer 130,the hole transport layer 140, the electron transport layer 160, and theelectron injection layer 170 may be omitted. The organic light-emittingdevice 100 may further include another layer. In addition, each layer ofthe organic light-emitting device 100 may be a single layer or amulti-layer.

A method of manufacturing each layer of the organic light-emittingdevice 100 according to the embodiment is not particularly limited. Forexample, each layer of the organic light-emitting device 100 accordingto the embodiment may be manufactured by using various methods, such asvacuum deposition, solution coating, and Langmuir-Blodgett (LB)deposition.

The solution coating may include spin coating, casting, micro gravurecoating, gravure coating, bar coating, roll coating, wire bar coating,dip coating, spry coating, screen printing, flexographic printing,offset printing, and ink-jet printing.

Examples of the solvent used in the solution coating may includetoluene, xylene, diethyl ether, chloroform, ethyl acetate,dichloromethane, tetrahydrofuran, acetone, acetonitrile,N,N-dimethylformamide, dimethylsulfoxide, anisole, hexamethylphosphoricacid triamide, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene,o-dichlorobenzene, dioxane, cyclohexane, n-pentane, n-hexane, n-heptane,n-octane, n-nonane, n-decane, methyl ethyl ketone, cyclohexanone, butylacetate, ethyl cellosolve acetate, ethylene glycol, ethylene glycolmonobutyl ether, ethylene glycol monoethyl ether, ethylene glycolmonomethyl ether, dimethoxy ethane, propylene glycol, diethoxymethane,triethylene glycol monoethyl ether, glycerine, 1,2-hexanediol, methanol,ethanol, propanol, iso-propanol, cyclohexanol, andN-methyl-2-pyrrolidone, but the solvent is not limited as long as thesolvent can dissolve the material used to form each layer.

Considering the coatability, the concentration of the composition usedin the solution coating may be in a range from 0.1 weight % to 10 weight%, and for example, in a range from 0.5 weight % to 5 weight %, butembodiments of the present disclosure are not limited thereto.

The compound used in the vacuum deposition may be different according tothe structure and thermal characteristics of the target layer, but maybe selected from, for example, a deposition temperature of about 100° C.to about 500° C., a vacuum degree of about 10⁻⁸ torr to about 10⁻³ torr,a deposition rate of about 0.01 Angstroms per second (Å/sec) to about100 Å/sec.

In an embodiment, the first electrode 120 may be an anode, and thesecond electrode 180 may be a cathode.

For example, the first electrode 120 may be an anode; the secondelectrode 180 may be a cathode; the organic layer may include theemission layer 150 between the first electrode 120 and the secondelectrode 180; the organic layer may further include a hole transportregion disposed between the first electrode 120 and the emission layer150 and an electron transport region disposed between the emission layer150 and the second electrode 180; the hole transport region may includeat least one selected from a hole injection layer 130, a hole transportlayer 140, a buffer layer, and an electron blocking layer; and theelectron transport region may include at least one selected from a holeblocking layer, an electron transport layer 160, and an electroninjection layer 170.

In one or more embodiments, the first electrode 120 may be a cathode,and the second electrode 180 may be an anode.

Hereinbefore, the organic light-emitting device has been described withreference to the FIGURE, but embodiments of the present disclosure arenot limited thereto.

Description of Substituents

The expression “X and Y may each independently be” as used herein refersto a case where X and Y may be identical to each other, or a case whereX and Y may be different from each other.

The term “substituted” as used herein refers to a case where hydrogen ofa substituent such as R₁₁ may be further substituted with othersubstituents.

The term “derived” as used herein refers to a case where a compound ismodified without changing the basic structure and properties of thecompound. For example, a group derived from an aromatic compoundmaintains the skeletal structure of the aromatic compound. In addition,a group derived from a given compound may be understood as an n-th groupin which hydrogen in the number of n is excluded from the givencompound.

The term “C₁-C₁₀ alkyl group” as used herein refers to a linear orbranched aliphatic hydrocarbon monovalent group having 1 to 10 carbonatoms, and non-limiting examples thereof include a methyl group, anethyl group, an n-propyl group, an iso-propyl group, an n-butyl group,an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentylgroup, an iso-pentyl group, a tert-pentyl group, a neo-pentyl group, a1,2-dimethylpropyl group, an n-hexyl group, an iso-hexyl group, a1,3-dimethylbutyl group, 1-iso-propylpropyl group, a 1,2-dimethylbutylgroup, an n-heptyl group, a 1,4-dimethylpentyl group, a 3-ethylpentylgroup, a 2-methyl-1-iso-propylpropyl group, a 1-ethyl-3-methylbutylgroup, an n-octyl group, a 2-ethylhexyl group,3-methyl-1-iso-propylbutyl group, a 2-methyl-1-iso-propyl group, a1-tert-butyl-2-methylpropyl group, an n-nonyl group, an n-decyl group,and an iso-decyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atomsinvolved in the ring formation, and examples thereof include acyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexylgroup, and a cycloheptyl group.

The term “aryl group having 5 to 60 ring-forming carbon atoms” as usedherein refers to a monovalent group having an carbocyclic aromaticsystem including 5 to 60 carbon atoms involved in ring formation (thatis, when substituted with a substituent, an atom included in thesubstituent is not counted as a ring-forming carbon). Non-limitingexamples of the aryl group having 6 to 60 ring-forming carbon atomsinclude a phenyl group, a naphthyl group, an anthracenyl group, aphenanthrenyl group, a pyrenyl group, and a chrysenyl group.

The term “heteroaryl group having 5 to 60 ring-forming atoms” as usedherein refers to a monovalent heterocyclic aromatic system having atleast one heteroatom selected from N, O, Si, P, and S as a ring-formingatom and 5 to 60 carbon atoms. Non-limiting examples of the heteroarylgroup having 5 to 60 ring-forming atoms include a pyridinyl group, apyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, and an isoquinolinyl group.

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed to each other, only carbonatoms as ring-forming atoms, and no aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic condensed polycyclicgroup include a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving the same structure as the monovalent non-aromatic condensedpolycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 2 to 60carbon atoms) having two or more rings condensed to each other, aheteroatom selected from N, O, P, Si, and S, other than carbon atoms, asa ring-forming atom, and no aromaticity in its entire molecularstructure. Non-limiting examples of the monovalent non-aromaticcondensed heteropolycyclic group include a carbazolyl group. The term“divalent non-aromatic condensed heteropolycyclic group” as used hereinrefers to a divalent group having the same structure as the monovalentnon-aromatic condensed heteropolycyclic group.

The term “carbocyclic group having 5 to 60 ring-forming carbon atoms” asused herein refers to a saturated or unsaturated cyclic group having, asa ring-forming atom, 5 to 60 carbon atoms only. The term “carbocyclicgroup having 5 to 60 ring-forming carbon atoms” as used herein refers toa monocyclic group or a polycyclic group, and, according to its chemicalstructure, a monovalent, divalent, trivalent, tetravalent, pentavalent,or hexavalent group.

The term “heterocyclic group having 5 to 60 ring-forming atoms” as usedherein refers to a saturated or unsaturated cyclic group having, as aring-forming atom, at least one heteroatom selected from N, O, P, Si,and S, in addition to a carbon atom, wherein the number of atomsinvolved in ring formation is 5 to 60. The term “C₅-C₆₀ heterocyclicgroup” as used herein refers to a monocyclic group or a polycyclicgroup, and, according to its chemical structure, a monovalent, divalent,trivalent, tetravalent, pentavalent, or hexavalent group.

At least one substituent of the substituted C₁-C₁₀ alkyl group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted aryl group having 6to 60 ring-forming carbon atoms, the substituted heteroaryl group having5 to 60 ring-forming atoms, the substituted monovalent non-aromaticcondensed polycyclic group, the substituted monovalent non-aromaticcondensed heteropolycyclic group, the substituted carbocyclic grouphaving 5 to 60 ring-forming carbon atoms, and the substitutedheterocyclic group having 5 to 60 ring-forming atoms may be selectedfrom:

-   -   deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H,        —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino        group, an amidino group, a hydrazine group, a hydrazone group, a        carboxylic acid group or a salt thereof, a sulfonic acid group        or a salt thereof, a phosphoric acid group or a salt thereof, a        C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group, and a C₁-C₆₀ alkoxy group;    -   a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl        group, and a C₁-C₆₀ alkoxy group, each substituted with at least        one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₃-C₁₀ cycloalkyl group, a        C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl        group, a monovalent non-aromatic condensed polycyclic group, a        monovalent non-aromatic condensed heteropolycyclic group,        —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), and        —P(═O)(Q₁₈)(Q₁₉);    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, and a monovalent non-aromatic        condensed heteropolycyclic group;    -   a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, and a monovalent non-aromatic        condensed heteropolycyclic group, each substituted with at least        one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H,        —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a        nitro group, an amino group, an amidino group, a hydrazine        group, a hydrazone group, a carboxylic acid group or a salt        thereof, a sulfonic acid group or a salt thereof, a phosphoric        acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀        alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a        C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a        C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a        C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio        group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic        condensed polycyclic group, a monovalent non-aromatic condensed        heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅),        —B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉); and    -   —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and        —P(═O)(Q₃₈)(Q₃₉), and    -   Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each        independently be selected from hydrogen, deuterium, —F, —Cl,        —Br, —I, a hydroxyl group, a cyano group, a nitro group, an        amino group, an amidino group, a hydrazine group, a hydrazone        group, a carboxylic acid group or a salt thereof, a sulfonic        acid group or a salt thereof, a phosphoric acid group or a salt        thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀        alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group,        a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a        C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀        aryl group substituted with at least one selected from a C₁-C₆₀        alkyl group, and a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a        C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent        non-aromatic condensed polycyclic group, and a monovalent        non-aromatic condensed heteropolycyclic group.

Others

The expression “A to B” as used herein refers to a range from A to B,including A and B.

While the embodiments of the present disclose have been described withreference to the accompanying drawings, it is understood that thepresent disclosure is not limited to these embodiments. It is apparentto those of ordinary skill in the art that various modifications orchanges may be made thereto without departing from the spirit and scopeof the appended claims. It is understood that various modifications orchanges fall within the technical scope of the present disclosure.

Hereinafter, a condensed cyclic compound represented by Formula 1 and anorganic light-emitting device including the same will be described indetail with reference to Examples and Comparative Examples. Examplesprovided below are merely an example, and the condensed cyclic compoundand the organic light-emitting device, according to embodiments, are notlimited to Examples provided below.

The expression “B was used instead of A” used in describing SynthesisExamples means that a molar equivalent of “A” was identical to a molarequivalent of “B”.

In addition, “%” is weight % unless specified otherwise.

EXAMPLES Synthesis Example 1: Synthesis of Compound 1-1

Compound 1-1 was synthesized according to the Reaction Scheme:

1) Synthesis of Intermediate A

In an argon atmosphere, 3-bromo-9H-carbazole (12.3 grams (g), 50 mmol,millimoles), 2-([1,1′:3′1′-terphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (18.0 g,50.5 mmol), tetrakis(triphenylphosphine)palladium (1.73 g, 1.50 mmol),100 milliliters (ml) of 1,2-dimethoxyethane, and 75 ml of 2 molar (M)aqueous sodium carbonate solution were added to a 200-ml three-neckflask, and the mixture was stirred at a temperature of 80° C. for 8hours. After the mixture was left at room temperature, impurities werefiltered and separated by using celite. The organic layer wasconcentrated and purified by column chromatography to obtainIntermediate A (14.6 g, 36.9 mmol, yield of 73.8%).

2) Synthesis of Intermediate B

In an argon atmosphere,2-(4′-chloro-[1,1′-biphenyl]-3-yl)dibenzo[b,d]furan) (3.35 g, 10.0mmol), Intermediate A (4.15 g, 10.5 mmol),tris(dibenzylideneacetone)dipalladium) (0.916 g, 1.00 mmol),tetrafluoroboric acid tri-t-butylphosphine (1.16 g, 4.00 mmol),sodium-t-butoxide (1.44 g, 15.0 mmol), and 30 ml of anhydrous xylenewere added to a 300-ml three-neck flask, and the mixture was stirred ata temperature of 120° C. for 4 hours. After the mixture was left at roomtemperature, impurities were filtered and separated by using celite. Theorganic layer was concentrated and purified by column chromatography toobtain Intermediate B (5.02 g, 7.03 mmol, yield of 70.3%).

3) Synthesis of Intermediate C

In an argon atmosphere, Intermediate B (5.00 g, 7.00 mmol) and 100 ml ofanhydrous tetrahydrofuran (THF) were added to a 300-ml three-neck flask,and the mixture was cooled to a temperature of −78° C. Then,n-butyllithium, 1.6 M hexane solution (n-butyllithium, 1.6 M in hexane)(6.6 ml, 10.5 mmol) were added dropwise thereto for 30 minutes. For 4hours after the dropwise addition, the mixture was maintained at atemperature of −78° C. and stirred. Then, 2.2 ml of2-iso-propoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added dropwisethereto, a reaction was allowed to proceed for 15 minutes, and themixture was stirred again at room temperature for 5 hours. Then, 100 mlof ion-exchange water was added thereto, the product was extracted byusing dichloromethane and recrystallized by using methanol to obtainIntermediate C (4.6 g, 5.48 mmol, yield of 78.2%).

4) Synthesis of Compound 1-1

In an argon atmosphere,2-(4′-bromo-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (0.99 g, 2mmol), Intermediate C (1.72 g, 2.05 mmol),tetrakis(triphenylphosphine)palladium (0.07 g, 0.06 mmol), 10 ml of1,2-dimethoxyethane, 10 ml of toluene, and 3 ml of 2 M aqueous sodiumcarbonate solution were added to a 100-ml three-neck flask, and themixture was stirred at a temperature of 100° C. for 8 hours. After themixture was cooled to room temperature, impurities were filtered andseparated by using celite. The organic layer was concentrated andpurified by column chromatography to obtain Compound 1-1 (1.10 g, 1.0mmol, yield of 50.0%).

A molecular weight (m/z value) of Compound 1-1 measured by LC-MS was1097 (M⁺), which was identical to a calculated value. The number ofaromatic rings in Compound 1-1 was 14.

Synthesis Example 2: Synthesis of Compound 1-2

Compound 1-2 was synthesized according to the Reaction Scheme:

A molecular weight (m/z value) of Compound 1-2 measured by LC-MS wasidentical to 1173 (M⁺), which was a calculated value. The number ofaromatic rings in Compound 1-2 was 15.

Evaluation Example 1: Measurement of Solubility

50 milligrams (mg) of Compound 1-1 and 450 mg of methyl benzoate(solvent) were added to a colorless sample bottle, the mixture wasirradiated with ultrasonic waves at room temperature for 5 minutes, andthe presence or absence of Compound 1-1 was visually confirmed. IfCompound 1-1 did not remain, the solubility of Compound 1-1 was 10percent by weight (weight %) or more. If Compound 1-1 remained, a smallamount of the solvent was added, the irradiation with ultrasonic waveswas repeated, and an amount of the solvent was measured until Compound1-1 was completely dissolved. The solubility was calculated from anamount of the solvent finally used. The solubility values of Compound1-2 and host-c were calculated in the same manner. The results are shownin Table 1.

TABLE 1 Solubility (weight %) Compound 1-1 4 Compound 1-2 4 host-c 0.1

Referring to Table 1, it is confirmed that Compounds 1-1 and 1-2 havehigh solubility in an organic solvent, as compared with host-c.Therefore, it is confirmed that Compound 1-1 and 1-2 are suitable formanufacturing an organic light-emitting device at a low cost, ascompared with host-c.

Example 1

Poly(3,4-ethylene dioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS)(manufactured by Sigma-Aldrich) were spin-coated on a glass substratehaving a 150-nm stripe-shaped ITO such that a thickness of a dried filmwas 15 nanometers (nm), thereby forming a hole injection layer.

Then, a solution in which P-1 and FA-14 were dissolved in anisole wasspin-coated on the hole injection layer such that a thickness of a driedfilm was 125 nm, thereby forming a hole transport layer. At this time,P-1 was 80 weight % based on a total weight of the hole transport layer,FA-14 was 20 weight % based on a total weight of the hole transportlayer.

Then, a methyl benzoate solution including Compound 1-1 (host),HT-Host-A (host), and tris(2-(3-p-xylyl)phenyl)pyridine iridium (TEG)(dopant) was spin-coated on the hole transport layer such that athickness of a dried film was 55 nm, thereby forming an emission layer.At this time, TEG was 10 weight % based on a total weight of theemission layer, and Compound 1-1 and HT-Host-A were at a weight ratio of5:5.

Then, the substrate on which the emission layer was formed wasintroduced into a vacuum evaporator, and LiQ and KLET-03 wereco-deposited at a volume ratio of 1:1, thereby forming an electrontransport layer having a thickness of 20 nm.

LiQ was deposited on the electron transport layer to form an electroninjection layer having a thickness of 3.5 nm.

Then, aluminum was deposited on the electron injection layer to form acathode having a thickness of 100 nm, thereby completing the manufactureof an organic light-emitting device.

P-1 was manufactured according to a method of preparing Compound T,disclosed in International Publication No. WO 2011/159872. Theconstitutional formula of P-1 is as follows:

Number average molecular weight M_(n)=141,000

Weight average molecular weight M_(w)=511,000

In addition, FA-14 is a compound disclosed in US Patent ApplicationPublication No. 2016/0315259, which is incorporated herein in itsentirety by reference, and the constitutional formula of FA-14 is asfollows:

HT-Host-A and HT-Host-B used in Examples 1 to 6 are hole transport hostmaterials.

In addition, the constitutional formula of TEG is as follows:

Examples 2 to 6 and Comparative Examples 1 and 2

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that an emission layer was changed to thecompositions shown in Table 2.

Evaluation Example 2

The current efficiency and light-emitting lifespan of the organiclight-emitting devices of Examples 1 to 6 and Comparative Examples 1 and2 were evaluated by using the following method. The organiclight-emitting device was caused to emit light by applying apredetermined voltage thereto by using a DC constant voltage powersupply (for example, Source Meter manufactured by KEYENCE). The lightemission of the organic light-emitting device was measured by using aluminance measurement device (for example, SR-3 manufactured by Topcom),a current was set to be constant when a luminance was 6,000 candelas persquare meter (cd/m²) while gradually increasing a current appliedthereto, and the organic light-emitting device was left.

Here, the current density (current value per unit area) of the organiclight-emitting device was calculated, and the “current efficiency(cd/A)” was calculated by dividing the luminance (cd/m²) by the currentdensity (amperes per square meter, A/m²).

In addition, the “light-emitting lifespan (LT₈₀, hr)” indicates anamount of time until the luminance value measured by using the luminancemeasurement device gradually decreased and becomes 80% of initialluminance.

These evaluation results are shown in Table 2.

The current efficiency and light-emitting lifespan of Examples 1 to 6and Comparative Examples 1 and 2 are relative values when the measuredvalues of Comparative Example 1 are 100.

TABLE 2 Light-emitting Host (weight ratio) Current efficiency lifespanExample 1 Compound 1-1:HT-Host-A (5:5) 128 360 Example 2 Compound1-1:HT-Host-A (7:3) 147 390 Example 3 Compound 1-2:HT-Host-A (5:5) 122300 Example 4 Compound 1-2:HT-Host-A (7:3) 139 325 Example 5 Compound1-1:HT-Host-B (5:5) 143 360 Example 6 Compound 1-1:HT-Host-B (2:8) 136500 Comparative host-a:host-b (5:5) 100 100 Example 1 Comparative host-cSince device could not be manufactured, Example 2 measurement wasimpossible.

Referring to Table 2, it is confirmed that the condensed cyclic compoundhas excellent characteristics in terms of the solubility to the solventand is suitable for the solution process.

In addition, it is confirmed that the OLEDs described in Examples 1 to 6have improved current efficiency and lifespan, as compared with thatdescribed in Comparative Example 1.

Since the condensed cyclic compound has improved electricalcharacteristics and/or thermal stability, the organic light-emittingdevice including the condensed cyclic compound has improved currentefficiency and lifespan characteristics.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope of the present disclosure as definedby the following claims.

What is claimed is:
 1. A condensed cyclic compound represented by oneselected from Formulae 1-1 to 1-6 and comprising 9 to 60 single6-membered aromatic rings:

wherein, in Formulae 1-1 to 1-6, L is selected from hydrogen, a singlebond, a substituted or unsubstituted carbocyclic group having 5 to 60ring-forming carbon atoms, and a substituted or unsubstitutedheterocyclic group having 5 to 60 ring-forming atoms, X₁₁, X_(11a), andX_(11b) are each independently an oxygen atom or a sulfur atom, a11,a12, a11a, a11b, a12a, and a12b are each independently selected from 0,1, 2, 3, and 4, wherein when a11 is 0, L₁₁ is a single bond, when a12 is0, L₁₂ is a single bond, when a11a is 0, L_(11a) is a single bond, whena11b is 0, L_(11b) is a single bond, when a12a is 0, L_(12a) is a singlebond, and when a12b is 0, L_(12b) is a single bond, L₁₁, L₁₂, L_(11a),L_(11b), L_(12a) and L_(12b) are each independently selected from asubstituted or unsubstituted carbocyclic group having 5 to 60ring-forming carbon atoms, and a substituted or unsubstitutedheterocyclic group having 5 to 60 ring-forming atoms, HT, HT_(a), andHT_(b) are each independently selected from a substituted orunsubstituted carbazole group, a substituted or unsubstitutedazacarbazole group, a substituted or unsubstituted benzocarbazole group,a substituted or unsubstituted hydrocarbazole group, a substituted orunsubstituted acridine group, a substituted or unsubstituted indolegroup, a substituted or unsubstituted xanthene group, a substituted orunsubstituted phenoxazine group, and a substituted or unsubstituteddiphenyl amine group, and two or more substituents included in HT areoptionally linked to form a ring, ET, ET_(a), and ET_(b) are eachindependently selected from a substituted or unsubstituted pyrrolegroup, a substituted or unsubstituted pyrazole group, a substituted orunsubstituted imidazole group, a substituted or unsubstituted triazolegroup, a substituted or unsubstituted pyridine group, a substituted orunsubstituted pyrimidine group, a substituted or unsubstitutedpyridazine group, a substituted or unsubstituted pyrazine group, asubstituted or unsubstituted triazine group, a substituted orunsubstituted indole group, a substituted or unsubstituted isoindolegroup, a substituted or unsubstituted indazole group, a substituted orunsubstituted benzimidazole group, a substituted or unsubstitutedquinoline group, a substituted or unsubstituted isoquinoline group, asubstituted or unsubstituted phthalazine group, a substituted orunsubstituted naphthyridine group, a substituted or unsubstitutedcinnoline group, a substituted or unsubstituted quinoxaline group, asubstituted or unsubstituted quinazoline group, and a substituted orunsubstituted imidazopyridine group, R₁₁ to R₁₈, R_(12a), R_(12b),R_(13a), R_(13b), R_(14a), R_(14b), R_(15a), R_(15b), R_(16a), R_(16b),R_(17a), R_(17b), R_(18a), and R_(18b) hydrogen, deuterium, asubstituted or unsubstituted phenyl group, a substituted orunsubstituted biphenyl group, a substituted or unsubstituted terphenylgroup, a substituted or unsubstituted tetraphenyl group, a substitutedor unsubstituted naphthyl group, a substituted or unsubstitutedfluorenyl group, a substituted or unsubstituted pyridinyl group, and asubstituted or unsubstituted pyrimidinyl group.
 2. The condensed cycliccompound of claim 1, wherein the condensed cyclic compound comprises 10to 30 single 6-membered aromatic rings.
 3. The condensed cyclic compoundof claim 1, wherein the condensed cyclic compound has a molecular weightof about 850 Daltons to about 3,000 Daltons.
 4. The condensed cycliccompound of claim 1, wherein HT, HT_(a) and HT_(b) are eachindependently selected from: a carbazole group, an azacarbazole group, abenzocarbazole group, a hydrocarbazole group, an acridine group, anindole group, a xanthene group, a phenoxazine group, and a diphenylamine group; and a carbazole group, an azacarbazole group, abenzocarbazole group, a hydrocarbazole group, an acridine group, anindole group, a xanthene group, a phenoxazine group, and a diphenylamine group, each substituted with at least one selected from deuterium,—F, —Cl, —Br, —I, a substituted or unsubstituted aryl group having 6 to60 ring-forming carbon atoms, and a substituted or unsubstitutedheteroaryl group having 5 to 60 ring-forming atoms, and two or moresubstituents included in HT_(a) and HT_(b) are optionally linked to forma ring.
 5. The condensed cyclic compound of claim 1, wherein HT, HT_(a)and HT_(b) are each independently represented by one selected fromFormulae 3-1 to 3-9:

wherein, in Formulae 3-1 to 3-9, X₃₁ is selected from 0 and C(R₃₄)(R₃₅),R₃₁ to R₃₅ are each independently selected from hydrogen, deuterium, —F,—Cl, —Br, —I, a substituted or unsubstituted aryl group having 6 to 60ring-forming carbon atoms, and a substituted or unsubstituted heteroarylgroup having 5 to 60 ring-forming atoms, two neighboring groups selectedfrom R₃₁ to R₃₅ are optionally linked to form a ring, b31 is selectedfrom 1, 2, 3, 4, and 5, b32 is selected from 1, 2, 3, and 4, b33 isselected from 1, 2, and 3, b34 is selected from 1 and 2, and * indicatesa binding site to a neighboring atom.
 6. The condensed cyclic compoundof claim 1, wherein ET, ET_(a) and ET_(b) are each independentlyselected from: a pyrrole group, a pyrazole group, an imidazole group, atriazole group, a pyridine group, a pyrimidine group, a pyridazinegroup, a pyrazine group, a triazine group, an indole group, an isoindolegroup, an indazole group, a benzimidazole group, a quinoline group, anisoquinoline group, a phthalazine group, a naphthyridine group, acinnoline group, a quinoxaline group, a quinazoline group, and animidazopyridine group; and a pyrrole group, a pyrazole group, animidazole group, a triazole group, a pyridine group, a pyrimidine group,a pyridazine group, a pyrazine group, a triazine group, an indole group,an isoindole group, an indazole group, a benzimidazole group, aquinoline group, an isoquinoline group, a phthalazine group, anaphthyridine group, a cinnoline group, a quinoxaline group, aquinazoline group, and an imidazopyridine group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a substituted orunsubstituted aryl group having 6 to 60 ring-forming carbon atoms, and asubstituted or unsubstituted heteroaryl group having 5 to 60ring-forming atoms.
 7. The condensed cyclic compound of claim 1, whereinET, ET_(a) and ET_(b) are each independently is a group represented byone selected from Formulae 2-1 to 2-4:

wherein, in Formulae 2-1 to 2-4, R₂₁ is selected from deuterium, —F,—Cl, —Br, —I, a substituted or unsubstituted aryl group having 6 to 60ring-forming carbon atoms, and a substituted or unsubstituted heteroarylgroup having 5 to 60 ring-forming atoms, two neighboring groups selectedfrom groups R₂₁ are optionally linked to form a ring, b21 is selectedfrom 1, 2, and 3, b22 is selected from 1 and 2, and * indicates abinding site to a neighboring atom.
 8. A composition comprising at leastone of the condensed cyclic compound of claim
 1. 9. The composition ofclaim 8, further comprising a light-emitting material.
 10. An organiclight-emitting device comprising: a first electrode; a second electrode;and an organic layer disposed between the first electrode and the secondelectrode, wherein the organic layer comprises an emission layer, andwherein the organic layer comprises at least one of the condensed cycliccompound of claim
 1. 11. The organic light-emitting device of claim 10,wherein the first electrode is an anode, the second electrode is acathode, and the organic layer further comprises a hole transport regiondisposed between the first electrode and the emission layer and anelectron transport region disposed between the emission layer and thesecond electrode, wherein the hole transport region comprises a holeinjection layer, a hole transport layer, an electron blocking layer, orany combination thereof, and wherein the electron transport regioncomprises a hole blocking layer, an electron transport layer, anelectron injection layer, or any combination thereof.
 12. The organiclight-emitting device of claim 10, wherein the emission layer comprisesthe condensed cyclic compound.
 13. The organic light-emitting device ofclaim 12, wherein the emission layer further comprises a light-emittingmaterial, and an amount of the condensed cyclic compound in the emissionlayer is larger than an amount of the light-emitting material in theemission layer.